Hilton Head Island and Bluffton Area Real Estate Search

Deepwater Homes for Sale

942 May River Road, Bluffton
$6,985,000
5 Beds ⋅ 5 Baths ⋅ 3,402 SqFt. ⋅ HILTONHEAD-504994 MLS
One of the last remaining legacy waterfront estates in Bluffton, this extraordinary property is being offered for the first time in 65 years. Encompassing 16.6 acres of high ground adorned with majestic trees and heirloom plantings, the estate boasts 485 feet of frontage along the scenic May River, with sweeping views both upriver and downriver. Accessed from picturesque South Carolina Highway 46, the property enjoys a prime location just minutes from downtown Bluffton, approximately 20 minutes to historic Savannah, and 30 minutes to charming Beaufort. The existing approximately 3,400-square-foot residence, built in the 1960s, offers the opportunity for restoration or the perfect footprint for a custom new build. A private dock and swimming pool enhance the waterfront lifestyle, while rare Old Line Camellia plantings add character and timeless Southern charm. With substantial acreage between May River Road and the riverfront, the estate offers exceptional privacy and flexibility-ideal for a multigenerational family compound, equestrian retreat, or legacy waterfront residence. A rare opportunity to secure one of Bluffton's most significant remaining riverfront properties.

942 May River Road, Bluffton

Listing courtesy of Charter One Realty.

J-159 Windmill Harbour Marina, Hilton Head Island
$134,000
HILTONHEAD-504233 MLS
Highly sought after 45' boatslip on the promenade in Windmill Harbour. Easy tide-free docking and constant 8' depth. Windmill Harbour Marina is a secure, protected harbour with a lock system. Immediate deep water access to the Calibogue Sound (Intra-Coastal Waterway) and convenient to Beaufort and Savannah. Enjoy the South Carolina Yacht Club which is just steps away.

J-159 Windmill Harbour Marina, Hilton Head Island

Listing courtesy of Windmill Harbour Real Estate.

70 Paddle Boat Lane Unit 303D, Hilton Head Island
$377,000
2 Beds ⋅ 2 Baths ⋅ 1,240 SqFt. ⋅ HILTONHEAD-502473 MLS
Lookіng for an affοrdаble Ηіltοn Hеаd Island condo with а Brοad Creek view? 303D Palmetto Bay Marina Villas offers 2BR/2BA and 1,240 sq ft of comfortable living space overlooking the marsh and Broad Creek, creating a beautiful Lowcountry backdrop from the private balcony. Currently the only 2BR condo offered under $400,000 with a Broad Creek view on Hilton Head, this property presents a compelling opportunity for a buyer seeking waterfront scenery without the typical waterfront price point. The villa has been well cared for with an updated HVAC system and hot water heater, while the interior offers an excellent opportunity to further personalize over time. Offered fully furnished for added convenience. Just steps away, Palmetto Bay Marina is home to popular restaurants and waterfront destinations including Black Marlin, with boating and water activities nearby. The location also provides convenient access on and off Hilton Head Island while keeping the beaches, shopping, dining, and entertainment of the south end within easy reach. Coligny Beach, Coligny Plaza, and Lowcountry Celebration Park are approximately 10 minutes away. Whether you're searching for a primary residence, second home, or Hilton Head getaway, 303D offers a rare combination of Broad Creek views, location, value, and future potential.

70 Paddle Boat Lane Unit 303D, Hilton Head Island

Listing courtesy of William Raveis - Carolina LLC.

11 Whiting Street, Bluffton
$639,000
3 Beds ⋅ 2 Baths ⋅ 1,350 SqFt. ⋅ HILTONHEAD-502029 MLS
11 Whiting Street is the quintessential Brighton Beach cottage, lovingly built circa 1945 and just a stones throw from the Alljoy boat landing. From the main living area, enjoy peaceful river views that perfectly capture the magic of this special Bluffton neighborhood. Tucked beneath the shade of a grand live oak, this sweet cottage invites easy mornings, sunrise strolls to the water, and the laid-back, eclectic lifestyle that makes this part of Bluffton so unique. Come "cut the beach" and make this slice of Lowcountry charm your own.

11 Whiting Street, Bluffton

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

170 Dillon Road, Hilton Head Island
$4,750,000
4 Beds ⋅ 5 Baths ⋅ 2,216 SqFt. ⋅ HILTONHEAD-500657 MLS
Incredible development opportunity on Hilton Head Island with the potential for 8 UNITS AN ACRE, featuring marsh and sound views with a designated beach walk easement. Four combined parcels span over four acres, offering rare potential for a private estate, multi-home enclave or workforce housing. The property adjoins historic Mitchellville Freedom Park, providing a unique setting rich in natural beauty and heritage. A gracious 2200 SF home with additional SF in separate barn and apartment (6000+ total finished SF on the property) already on-site can serve as a primary residence, creating a sprawling private compound, or function as a clubhouse for future residences. Whether envisioned as a legacy property or an investment in a premier coastal destination, this offering presents unmatched possibilities in one of Hilton Heads most desirable locations.

170 Dillon Road, Hilton Head Island

Listing courtesy of Sea Pines Real Estate - Beach Club.

6 Lighthouse Lane Unit 953, Hilton Head Island
$1,299,000
3 Beds ⋅ 2 Baths ⋅ 1,400 SqFt. ⋅ HILTONHEAD-500129 MLS
This highly sought-after Cutter Court Penthouse in the heart of Sea Pines, with its jaw-dropping direct views of the iconic Harbour Town Lighthouse, world-famous Harbour Town Marina, and the shimmering Calibogue Sound, is fully furnished and move-in ready. These penthouses rarely hit the market and sell quickly. This 3BR/2BA retreat has been completely updated and offers the perfect blend of style, comfort, and convenience, along with a strong short-term rental history. The spacious open layout includes a modern kitchen with granite countertops, stainless steel appliances, a dinette, and a bright living area. Relax and take in unforgettable sunsets from the main balcony, showcasing postcard-perfect views of the Lighthouse, Yacht Basin, and Calibogue Sound. The king master suite boasts its own private balcony, while two additional queen bedrooms offer comfort for family or guests. The two bathrooms each feature a walk-in shower, and the many windows throughout the Penthouse provide awesome views and abundant natural light. Its prime location puts you just steps from the Harbour Town Golf Links & Clubhouse, the Sea Pines Racquet Club, waterfront dining at the Quarterdeck and other popular restaurants, as well as charming shops, boutiques, art galleries, and the iconic Lighthouse itself. Enjoy world-class golfing in Sea Pines at the the three championship courses: Harbour Town Golf Links, Heron Point by Pete Dye and Atlantic Dunes by Davis Love III. Additional amenities include tennis and pickleball, Lawton Stables, Sea Pines Forest Preserve, Sea Pines Beach Club with private beach access, South Beach Marina, miles of bike trails, Sea Pines Center, and the free seasonal trolley service. Harbour Town is the vibrant heart of Hilton Head Island, alive with festivals, live music, shops, dining, and endless water activities all year long. Whether you're seeking a high-income short-term rental, a luxurious second home, or a permanent retreat, this Penthouse delivers it all - a prime location, top-floor privacy, as well as designer finishes and low-maintenance living in one of the Islands most prestigious addresses. Don't miss this chance to own a true Harbour Town gem where every day feels like a vacation.

6 Lighthouse Lane Unit 953, Hilton Head Island

Listing courtesy of Premier Properties of Hilton Head Island.

86 Meridian Point Drive, Bluffton
$1,250,000
HILTONHEAD-452321 MLS
Privatеly held for 80 уrѕ, NΟW іѕ yοur οpportunity to own аn untouсhed piece of history with soaring oaks and abundant wildlife. This 33.68acre estate with private island is located The Crescent. Parcel includes a stunning 1.9acre private island, providing unparalleled privacy & natural beauty. Surrounded by serene waters of the Colleton River, it boasts breathtaking water views and a blank canvas of endless possibilities for your dream home. This tremendous lot pays only one HOA Fee! Premium amenities, including a top-rated Arnold Palmer golf course, community pool, tennis, pickleball, club house, and more. Located only 3 miles to Hilton Head and a short drive to downtown Savannah.

86 Meridian Point Drive, Bluffton

Listing courtesy of William Raveis - Carolina LLC.

F-10 Boatslip Windmill Harbour, Hilton Head Island
$175,000
HILTONHEAD-452924 MLS
Rare 50 ft. slіp adjасent tο thе рromеnаde directly acrοsѕ from the South Carolina Yacht Club. Easy docking, great location and convenient to the lock. Enjoy safety and security in the Harbour at all times.

F-10 Boatslip Windmill Harbour, Hilton Head Island

Listing courtesy of Windmill Harbour Real Estate.

J-163 Windmill Harbour Marina, Hilton Head Island
$139,500
HILTONHEAD-452607 MLS
45 ft. boatslіp in Windmіll Ηarbοur Μаrinа. Τide-free lock hаrbour. Ηome of the South Carolina Yacht Club.

J-163 Windmill Harbour Marina, Hilton Head Island

Listing courtesy of Windmill Harbour Real Estate.

47 Pine View Drive, Bluffton
$2,675,000
4 Beds ⋅ 3 Baths ⋅ 3,552 SqFt. ⋅ HILTONHEAD-451323 MLS
Stunning pаrk-like ѕеtting аlοng thе shοrеs of the May Rivеr and Rοse Dhu Creek. A lovingly cared for home with renovations done throughout the many years of current ownership in addition to a recently rebuilt dock with deepwater access. Boasting over two acres filled with specimen hardwoods, the setting and views are nearly unparalleled. The community of May River Plantation is conveniently located just minutes from downtown Bluffton and has a rare and coveted private boat launch and day dock in place.

47 Pine View Drive, Bluffton

Listing courtesy of Daniel Ravenel Sotheby's International Realty.

103 Palmetto Bluff Road, Bluffton
$899,000
HILTONHEAD-442039 MLS
Rare 8.48-acre marshfront property with a peninsula overlooking Stoney Creek of the May River, featuring an existing private dock permit. Income-producing tenants provide immediate revenue while offering exceptional flexibility for a future private estate or investment hold. Expansive marsh views, privacy, and significant long-term potential make this one of the Lowcountry's most unique marshfront properties.

103 Palmetto Bluff Road, Bluffton

Listing courtesy of COAST PROFESSIONALS Brokered by EXP Realty.

Start Your Search
board logo

We do not attempt to independently verify the currency, completeness, accuracy or authenticity of the data contained herein. It may be subject to transcription and transmission errors. Accordingly, the data is provided on an “as is” “as available” basis only and may not reflect all real estate activity in the market. © 2026 REsides, Inc. All rights reserved. Certain information contained herein is derived from information, which is the licensed property of, and copyrighted by, REsides, Inc.

How much is your home worth?

Get instant property value now!